Day: November 17, 2022

Dong, Yanan published the artcileReductive cyanation of organic chlorides using CO2 and NH3 via Triphos-Ni(I) species, Application In Synthesis of 41910-64-9, the main research area is nitrile preparation; chloride organic reductive cyanation.

The reductive cyanation of organic chlorides RCl (R = C6H5, naphthalen-1-yl, cyclohexyl, etc.) using CO2/NH3 as the electrophilic CN source has been described. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products RCN in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Nature Communications published new progress about Antiproliferative agents. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Application In Synthesis of 41910-64-9.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nishiyama, Takashi published the artcileConcise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells, Application In Synthesis of 136818-66-1, the main research area is carbazolequinone preparation antiproliferative human; indole allyl alc tandem ring closing metathesis dehydrogenation; Antiproliferative activity; Carbazole-1,4-quinone; Koeniginequinone A; Koeniginequinone B.

A convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step is reported. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions I (R1 = R2 = H, CH3; R3 = H, 6-OCH3, 5,6-(OCH3)2, 7-CH3, 6-NO2, etc.; R4 = H, MOM) have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

European Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Application In Synthesis of 136818-66-1.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

See, Cheng Shang published the artcileDiscovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131), Application of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is indolyl isoquinolinyl acrylonitrile analogs preparation cancer mitosis autophagy; Antimitotic; Antiproliferative; Antitumor; Tumor-selective.

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20mg/kg IP twice a day.

European Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Application of N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Maddela, Srinubabu published the artcileSynthesis of isatin-quinoline conjugates as possible biologically active agents, Recommanded Product: 4,5-Dichloroisatin, the main research area is isatin quinoline conjugate preparation antibacterial antifungal antiinflammatory; quinolinyl hydrazide isatin condensation.

A series of 12 new quinoline-3-carbohydrazide derivatives I (R = H, 5-F, 4-Cl, 7-Cl, etc.) were synthesized by the condensation of quinolinyl hydrazide with different isatins. The synthesized compounds were evaluated for in vitro antimicrobial and in vivo anti-inflammatory activity. Tested compounds exhibited moderate to good antibacterial and antifungal activity. Evaluation of the compounds revealed remarkable anti-inflammatory activity and were comparable with standard, indomethacin. Compounds I (R = 5-O2N, 5-F, 7-Cl, 4-Cl) inhibited paw edema in a carrageenan-induced rat hind paw edema model.

Toxicological & Environmental Chemistry published new progress about Anti-inflammatory agents. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Recommanded Product: 4,5-Dichloroisatin.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Saczewski, Franciszek published the artcile1-[(Imidazolin-2-yl)amino]indoline and 1-[(imidazolin-2-yl)amino]1,2,3,4-tetrahydroquinoline derivatives: new insights into their circulatory activities, Category: indole-building-block, the main research area is imidazolinylamino indoline hydrochloride preparation mol modeling imidazoline adrenoceptor antihypertensive; quinoline imidazolinylamino hydrochloride preparation mol modeling imidazoline adrenoceptor antihypertensive.

N-[(Imidazolinyl)amino]indoline-hydrochlorides I·HCl [R = H, 2-CH3, 7-CH3, 4-Cl] and N-[(imidazolinyl)amino]tetrahydroquinoline-hydrochlorides II·HCl [R = H, 8-CH3] were synthesized and tested in vitro for their affinities to α1 and α2-adrenoceptors as well as imidazoline I1 and I2 receptors. The compounds most potent at either α1 or α2-adrenoceptors were administered i.v. to normotensive Wistar rats to determine their effects on mean arterial blood pressure and heart rate. Upon i.v. administration at dose of 0.1 mg/kg to normotensive male Wistar rats, the initial transient pressor effect was followed by long-lasting hypotension and bradycardia. The results revealed that the synthesized compounds I and II were found to possess circulatory profile characteristic of the centrally acting clonidine-like hypotensive imidazolines.

Acta Poloniae Pharmaceutica published new progress about Adrenoceptor antagonists. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Category: indole-building-block.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chou, Pi-Tai published the artcileExcited-State Double Proton Transfer in 3-Formyl-7-azaindole: Role of the nπ* State in Proton-Transfer Dynamics, Category: indole-building-block, the main research area is excited state double proton transfer dynamics formylazaindole hydrogen bonding.

3-Formyl-7-azaindole (3FAI) and its derivatives have been synthesized to study the role of the nπ* state in the excited-state double proton transfer (ESDPT) reaction. In 3FAI monomer as well as its associated hydrogen-bonded complexes the lowest excited singlet state has been concluded to be in the 1nπ* configuration. The association constants incorporating the hydrogen bonding formation were determined to be 1.9 × 104 (313 K), 2.2 × 104 (298 K) and 1.8 × 105 M-1 (298 K) for 3FAI dimer, 3FAI/azacyclohexanone and 3FAI/acetic acid, resp., in cyclohexane. In alcs., the rate of solvent (e.g., methanol) diffusional migration, forming a “”correct”” precursor for ESDPT, is concluded to be much slower than the rate of Sππ* → Snπ* internal conversion which has been deduced to be 4.37 × 1012 s-1. ESDPT is prohibited in the Snπ* state of which the relaxation dynamics are dominated by the rate of Snπ* → Tππ* intersystem crossing. In contrast, for 3FAI dimer or 3FAI/acetic acid complex possessing intact dual hydrogen bonds the intrinsic ESDPT is competitive with the rate of Sππ* → Snπ* internal conversion, resulting in a prominent imine-like tautomer emission. The results provide the first model among 7-azaindole analogs in which the fast rate of Sππ* → Snπ* internal conversion serves as an internal clock to examine the mechanism of guest mols. (including the bulk alcs.) assisted ESDPT.

Journal of Physical Chemistry A published new progress about Density functional theory. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Category: indole-building-block.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Fuller, Janis J. published the artcileBiosynthesis of violacein, structure and function of L-tryptophan oxidase VioA from Chromobacterium violaceum, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is tryptophan oxidase Chromobacterium structure function inhibitor substrate analog preparation; crystal structure tryptophan oxidase Chromobacterium; SAXS tryptophan oxidase Chromobacterium; L-tryptophan oxidase; crystal structure; enzyme mechanism; enzyme-inhibitor complex; flavoprotein; redox chemistry; site-directed mutagenesis; substrate specificity; violacein.

Violacein is a natural purple pigment of Chromobacterium violaceum with potential medical applications as antimicrobial, antiviral, and anticancer drugs. The initial step of violacein biosynthesis is the oxidative conversion of L-tryptophan into the corresponding α-imine catalyzed by the flavoenzyme, L-tryptophan oxidase (VioA). A substrate-related (3-(1H-indol-3-yl)-2-methylpropanoic acid) and a product-related (2-(1H-indol-3-ylmethyl)prop-2-enoic acid) competitive VioA inhibitor was synthesized for subsequent kinetic and x-ray crystallog. investigations. Structures of the binary VioA·FADH2 and of the ternary VioA·FADH2·2-(1H-indol-3-ylmethyl)prop-2-enoic acid complex were resolved. VioA formed a “”loosely associated”” homodimer as indicated by SAXS experiments VioA belongs to the glutathione reductase family 2 of FAD-dependent oxidoreductases according to the structurally conserved cofactor binding domain. The substrate-binding domain of VioA was mainly responsible for the specific recognition of L-tryptophan. Other canonical amino acids were efficiently discriminated with a minor conversion of L-phenylalanine. Furthermore, 7-aza-tryptophan, 1-methyl-tryptophan, 5-methyl-tryptophan, and 5-fluoro-tryptophan were efficient substrates of VioA. The ternary product-related VioA structure indicated involvement of protein domain movement during enzyme catalysis. Extensive structure-based mutagenesis in combination with enzyme kinetics (using L-tryptophan and substrate analogs) identified Arg-64, Lys-269, and Tyr-309 as key catalytic residues of VioA. An increased enzyme activity of protein variant H163A in the presence of l-phenylalanine indicated a functional role of His-163 in substrate binding. The combined structural and mutational analyses led to a detailed understanding of VioA substrate recognition. Related strategies for the in vivo synthesis of novel violacein derivatives were discussed.

Journal of Biological Chemistry published new progress about Chromobacterium violaceum. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Tong, Kun published the artcileVisible-Light-Induced Direct Oxidative C-H Amidation of Heteroarenes with Sulfonamides, Related Products of indole-building-block, the main research area is heterocyclic compound preparation regioselective photochem; heteroarene sulfonamide oxidative carbon hydrogen amidation iridium catalyst; C−H amidation; heterocycles; nitrogen-centered radicals; photochemistry; visible light.

A direct oxidative C-H amidation of heteroarenes, e.g., I, with sulfonamides RNHSO2R1 [R = CH3, C6H5, oxan-4-yl, etc.; R1 = CH3(CH2)4, C6H5, c-C3H5, pyridin-3-yl, etc.] via nitrogen-centered radicals has been described. Nitrogen-centered radicals are directly generated from oxidative cleavage of NH bonds under visible-light photoredox catalysis. Sulfonamides, which are easily accessed, used as tunable nitrogen sources. Bleach (aqueous NaClO solution), which is clean and economic, was used as the solely oxidant. A variety of heteroarenes, including indoles, pyrroles, and benzofurans, can undergo this amidation with high yields (up to 92%). These reactions are highly regioselective, and all the products, e.g., II, are isolated as single regioisomer.

Chemistry – A European Journal published new progress about Amidation (regioselective). 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Related Products of indole-building-block.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ranasinghe, Nadeesha published the artcileExtending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry, Safety of Methyl 6-nitro-1H-indole-2-carboxylate, the main research area is Hemetsberger Knittel indole synthesis microwave chem.

Microwave, flow and combination methodologies were applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodol. allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chem., allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.

Bioorganic & Medicinal Chemistry Letters published new progress about [3+2] Cycloaddition reaction. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, Safety of Methyl 6-nitro-1H-indole-2-carboxylate.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Liang, Taoyuan published the artcileStraightforward access to novel indolo[2,3-b]indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles, HPLC of Formula: 13523-93-8, the main research area is diarylamino indoloindole chemoselective preparation; diarylamine indole aerobic annulation copper catalyst.

An unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles was reported, which allowed direct access to novel 2-diarylamino-indolo[2,3-b]indoles I [R = Ph, 4-MeC6H4, 4-ClC6H4, etc.; R1 = Me, Et, Bn, etc.; R2 = H, 4-Me, 6-F, etc.; Ar = Ph, 4-MeC6H4, 4-t-BuC6H4, etc.; Ar1 = Ph, 4-MeC6H4], a class of potential photoelec. device mols. The developed transformation proceeded with broad substrate scope, good functional group tolerance, high chemo-selectivity and no need for pre-preparation of specific agents, which offered a practical route for diverse and atom-economic synthesis of the desired products.

Chemical Communications (Cambridge, United Kingdom) published new progress about [3+2] Cycloaddition reaction. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, HPLC of Formula: 13523-93-8.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles